Hydrochloric Acid → HCID 57671884, compound

HRID 1182769Notes

Reaction equation

HRID 1182769 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:12]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])=[CH:13][CH:14]=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]([CH3:23])([CH3:22])[NH:16]2)=O.Cl>O1CCCC1.O.C(OCC)(=O)C>[OH:8][CH2:9][C:11]1[C:12]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])=[CH:13][CH:14]=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]([CH3:22])([CH3:23])[NH:16]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 57672002HCID 57672002, compound

Product 1

HCID 57671884HCID 57671884, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
-10 °C

Procedure

Lithium aluminium hydride (753 mg, 19.8 mmol) was suspended in anhydrous tetrahydrofuran (60 mL) under nitrogen atmosphere. An anhydrous tetrahydrofuran solution (20 mL) of 8-methoxycarbonyl-7-(2-methoxy-4-methoxymethoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 8-6, 4.87 g, 12.2 mmol) was added dropwise thereto at −10° C., and stirred for 40 minutes at the same temperature. After ethyl acetate (10 mL), water (10 mL), and 2N aqueous HCl solution (15 mL) were added to the reaction mixture successively, ethyl acetate (300 mL) were added thereto. Water (300 mL) was added and the whole was partitioned. The organic layer was washed with saturated brine (400 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (1.86 g) as a yellow solid. (Yield 41%)

Workup

  1. customthe whole was partitioned
  2. washThe organic layer was washed with saturated brine (400 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-911659786a42449c9c2d74b2d086c94b
Source dataset
uspto-grants-2014_03
Patent number
US08664221B2

Reaction notes

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